Received 21 April 2011
aDokuz Eylül University, Faculty of Arts and Sciences, Department of Chemistry, Tinaztepe, 35160 Buca, Izmir, Turkey,bKarabük University, Department of Physics, 78050, Karabük, Turkey, and cHacettepe University, Department of Physics, 06800 Beytepe, Ankara, Turkey
Correspondence e-mail: firstname.lastname@example.org
In the title compound, C24H15NO2, the oxazole ring is oriented at dihedral angles of 10.09 (4) and 6.04 (4)° with respect to the mean planes of the naphthalene ring systems, while the two naphthalene ring systems make a dihedral angle of 4.32 (3)°. Intramolecular C-HN hydrogen bonds link the oxazole N atom to the naphthalene ring systems. In the crystal, intermolecular weak C-HO hydrogen bonds link the molecules into centrosymmetric dimers. - contacts between the oxazole and naphthalene rings and between the naphthalene ring systems [centroid-centroid distances = 3.5947 (9) and 3.7981 (9) Å] may further stabilize the crystal structure. Three weak C-H interactions also occur.
For the roles of oxazolones in the syntheses of amino acids, peptides, antimicrobial or antitumor compounds, immunomodulators, heterocyclic precursors for biosensors coupling and/or photosensitive composition devices for proteins, see: Gottwald & Seebach (1999); Meiwes et al. (1997); Martinez et al. (1964); Gelmi et al. (1997); Croce et al. (1994); Cannella et al. (1996); Kojima et al. (1998). For applications of the 5-oxazolones, including their use in semiconductor devices because of their promising photophysical and photochemical activity, see: Gündogdu et al. (2010). For bond-length data, see: Allen et al. (1987).
Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5196 ).
The authors are indebted to Anadolu University and the Medicinal Plants and Medicine Research Centre of Anadolu University, Eskisehir, Turkey, for the use of the diffractometer.
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cannella, R., Clerici, F., Gelmi, M. L., Penso, M. & Pocar, D. (1996). J. Org. Chem. 61, 1854-1856.
Croce, P. D., Ferraccioli, R. & Rosa, C. L. (1994). J. Chem. Soc. Perkin Trans. 1, pp. 2499-2502.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Gelmi, M. L., Clerici, F. & Melis, A. (1997). Tetrahedron, 53, 1843-1854.
Gottwald, K. & Seebach, D. (1999). Tetrahedron, 55, 723-738.
Gündogdu, C., Topkaya, D., Öztürk, G., Alp, S. & Ergün, Y. (2010). J. Heterocycl. Chem. 47, 1450-1453.
Kojima, S., Ohkawa, H., Hirano, T., Maki, S., Niwa, H., Ohashi, M., Inouye, S. & Tsuji, F. I. (1998). Tetrahedron Lett. 39, 5239-5242.
Martinez, A. P., Lee, W. W. & Goodman, L. (1964). Tetrahedron, 20, 2763-2771.
Meiwes, J., Schudock, M. & Kretzschmar, G. (1997). Tetrahedron Asymmetry, 8, 527-536.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.